EP0319911B1 - Structure laminée - Google Patents

Structure laminée Download PDF

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Publication number
EP0319911B1
EP0319911B1 EP88120354A EP88120354A EP0319911B1 EP 0319911 B1 EP0319911 B1 EP 0319911B1 EP 88120354 A EP88120354 A EP 88120354A EP 88120354 A EP88120354 A EP 88120354A EP 0319911 B1 EP0319911 B1 EP 0319911B1
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EP
European Patent Office
Prior art keywords
group
laminated structure
general formula
layer
organosilicon compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP88120354A
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German (de)
English (en)
Other versions
EP0319911A2 (fr
EP0319911A3 (en
Inventor
Tsuyoshi Baba
Akio Takigawa
Naoto Hirayama
Motoaki Yoshida
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Nippon Sheet Glass Co Ltd
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Nippon Sheet Glass Co Ltd
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Publication date
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Publication of EP0319911A3 publication Critical patent/EP0319911A3/en
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/10009—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/306—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl acetate or vinyl alcohol (co)polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
    • C08J5/125—Adhesives in organic diluents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2329/00—Polyvinylalcohols, polyvinylethers, polyvinylaldehydes, polyvinylketones or polyvinylketals
    • B32B2329/06—PVB, i.e. polyinylbutyral
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2367/00—Polyesters, e.g. PET, i.e. polyethylene terephthalate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/28—Non-macromolecular organic substances
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31627—Next to aldehyde or ketone condensation product
    • Y10T428/3163—Next to acetal of polymerized unsaturated alcohol [e.g., formal butyral, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31652—Of asbestos
    • Y10T428/31663—As siloxane, silicone or silane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]

Definitions

  • This invention relates to a laminated structure useful in a safety glass comprising a glass layer and a plastic layer laminated to each other.
  • the safety glass is used, for example, as a windshield of an automobile and a windowpane of a building.
  • flame treatment corona discharge treatment, ultraviolet treatment, plasma treatment, alkali treatment and treatment with various chemicals are known as a method of improving the adhesion of a polyester film.
  • Japanese Laid-Open Patent Publications Nos. 46717/1975, 19314/1978 and 219053/1985 and Japanese Patent Publication No. 37155/1983 propose methods in which the surface of a polyethylene terephthalate film is subjected to a flame treatment.
  • Japanese Laid-Open Patent Publication No. 176831/1987 propose a method of improving adhesion by providing a titanium dioxide between the polyester film and the polyvinylbutyral sheet.
  • 16344/1985 proposes a method of improving the adhesion between a polyester film and an organopolysiloxane compound layer by using an adhesive composed of a mixture of 3-(2-aminoethylamino)-propyltrimethoxysilane and an epoxy resin.
  • the above-cited Papers Read in the 30th Meeting of Polymer Research (Kobe), page 34 proposes a hexamethylenediamine as a surface-treating agent for polyester films.
  • the above-cited Collection of Articles on Polymers, vol. 35, 229 (1978) proposes hydrazine as a surface-treating agent for polyester films.
  • the flame treatment, corona discharge treatment, plasma treatment and alkali treatment undesirably result in a reduction in film strength.
  • the present inventors made extensive investigations in order to eliminate these defects of the prior art, and have now found that in a laminated structure of a polyester film and a polyvinylbutyral sheet, the adhesion between the laminated layers can be improved with good productivity by providing a layer of a specific organic compound between the polyester film and the polyvinylbutyral sheet.
  • a polyester film having a thickness of 10 to 500 micrometers is preferably used as the layer (A) comprising a polyester resin.
  • This polyester film may be, for example, a biaxially stretched film of a saturated polyester such as polyethylene terephthalate or polybutylene terephthalate.
  • the layer (C) comprising a polyvinylbutyral resin used in this invention is preferably a polyvinylbutyral sheet having a thickness of 300 to 1,500 micrometers.
  • the polyvinylbutyral sheet may contain plasticizers such as triethylene glycol di-2-ethylbutyrate, dihexyl adipate, triethylene glycol di-n-heptanoate, tetraethylene glycol di-n-heptanoate and propylene oxide oligomers and mixtures of these and other plasticizers known in the art.
  • amino group-containing organosilicon compounds of formula (I) used in the layer (B) in this invention include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, 2-(2-aminodiethylthio)-ethyltriethoxysilane, 2-(2-aminoethylthio)-ethyldiethoxymethylsilane, 3-(2-aminoethylamino)-propyltrimethoxysilane, 3-(2-aminoethylamino)-propyldimethoxymethylsilane, N-(3-triethoxysilylpropyl)-urea, and 3-[2-(2-aminoethylamino)-ethylamino]-propyltrimethoxysilane. They may be used either singly
  • Examples of the amine of general formula (II) used in the layer (B) in this invention are hydrazine, trimethylenediamine, tetramethylenediamine, hexamethylenediamine, dodecamethylenediamine and phenylenediamine. They may be used singly or in combination.
  • the mixing ratio between the organosilicon compound of general formula (I) and the diamine of general formula (II) is such that the proportion of the organosilicon compound of general formula (I) is 10 to 100 % by weight, pereferably 20 to 90 % by weight, more preferably 50 to 90 % by weight, most preferably 70 to 90 % by weight, based on the total weight of the organosilicon compound and the diamine of general formula (II). If the proportion of the organosilicon compound of general formula (I) is less than 10 % by weight, the adhesion strength between the layers (A) and (C) is lowered. If it exceeds 95 % by weight, the above adhesion strength at low temperatures is reduced.
  • the layer (B) in this invention can be conveniently formed by preparing a solution containing the organosilicon compound of general formula (I) and the diamine of general formula (II), coating the solution on one surface of the layer (A), and curing the coating under heat.
  • a water-soluble organic solvent such as methanol, ethanol, isopropanol, butanol, acetone, methyl Cellosolve, ethyl Cellosolve, propylene glycol monomethyl ether or dipropylene glycol monomethyl ether or water may, for example, be used as a solvent for preparing the solution.
  • the solvent may be applied by coating methods generally used, for example by roll coating, bar coating, dip coating, flow coating or spray coating.
  • the curing of the coating on the layer (A) may be performed at 100 to 150 °C for 1 to 5 minutes.
  • the thickness of the layer (B) is desirably not more than 1.0 micrometer.
  • the laminated structure of the invention can be obtained by laminating a polyvinylbutyral sheet to the layer (B) formed on the layer (A).
  • a glass laminated structure may be obtained by applying a glass sheet to the polyvinylbutyral sheet layer (C) of this laminated structure and treating the assembly under pressure at 40 to 150 °C for 10 to 60 minutes.
  • the surface of the glass or the surface of the polyvinylbutyral layer to be bonded to the glass may be treated with a silane coupling agent.
  • the polyester film generally has a low surface hardness and poor scratch resistance, its surface hardness should be improved. This may be achieved by using an organosiloxane-type hard coating agent or an acrylic hard-coating which is generally known.
  • the hydrolytic condensation product of the amino group-containing organosilicon compound of general formula (I) can be obtained by adding a small amount of water to the amino group-containing organosilicon compound of general formula (I) and allowing hydrolysis to take place.
  • the amount of water used in the hydrolysis is 0.01 to 10 % by weight, preferably 0.05 to 8 % by weight, more referably 0.1 to 5 % by weight. If the amount of water is less than 0.05 % by weight, variations of adhesion among production lots are great and the adhesion is not so good. If it is larger than 10 % by weight, the haze of the adhesive layer increases and becomes whitened.
  • the adhesive layer (B) resulting from curing of a composition comprising the amino group-containing organosilicon compound of general formula (I) or its hydrolytic condensation product and the diamine of general formula (II) has good adhesion to both of the polyester film and the polyvinylbutyral sheet over a broad temperature range, and acts as an adhesion improving layer for the polyester film and the polyvinylbutyral sheet.
  • the hydrolytic condensation product of the compound (II) is used, there is no variation in adhesion strength among lots.
  • the laminated structure of the invention when used in a safety glass, a sufficient adhesion strength is imparted between the polyester film and the polyvinylbutyral sheet which are important in an automobile windshield glass for preventing injury to a human body at the time of collision.
  • an automobile windshield glass of high safety can be obtained by the present invention.
  • Examples and Comparative Examples illustrate the laminated structure of the invention with reference to an adhesive layer resulting from the use of 3-aminopropyltriethoxysilane or 3-(2-aminoethylamino)-propyltrialkoxysilane and hexamethylenediamine as examples.
  • the invention is not limited to these examples. In these examples, all parts and percentages are by weight.
  • This polyethylene terephthalate film had been coated at the opposite surface with the organopolysiloxane-type hard coating agent described in Example 2 of Japanese Laid-Open Patent Publication No. 27740/1987. Then, a polyvinylbutyral sheet having a thickness of 380 micrometers was laid on the adhesive surface of the adhesive layer on the polyester film, and a glass sheet was laminated to that surface of the polyvinylbutyral sheet to which the polyester film was not bonded. The laminated structure was put in an autoclave and kept at 10 kg/cm2 and 150 °C for 30 minutes.
  • the adhesion properties of the resulting structure were evaluated by the following methods.
  • the polyethylene terephthalate film was peeled off from the polyvinylbutyral sheet parallel to the surface of the glass sheet, and the strength of adhesion at this time was examined and rated as follows:-
  • a 180 ° peel test was carried out at 23 °C and 0 °C respectively by an autograph (DCS-500 made by Shimadzu Seisakusho Co., Ltd.).
  • Table 1 Run Mixing proportion Adhesion (1) Hydrolytic condensation product of A-1100 (%) HMDA (%) 23 °C 0 °C Example 1 100 0 A B Comparative Example 1 0 100 C C Comparative Example 2 0 0 C C xample 2 50 50 A A-B Table 2 Run Mixing proportion Adhesion (1) (kg/25 mm) Hydrolytic condensation product of A-1100 (%) HMDA (%) 23 °C 0 °C Example 1 100 0 4.0 0.8 Example 2 50 50 4.5 1.4 Example 3 80 20 4.5 1.5 Example 4 20 80 4.5 1.5 Example 5 10 90 4.2 1.0
  • a polyvinylbutyral sheet was laid over a corona-discharge treated surface of a polyester film (T-50 type, a product of Toray Inc.), and by the same procedure as above, a laminated structure was produced.
  • the resulting structure showed an adhesion strength of 2 kg/25 mm at 23 °C and 0 kg/25 mm at 0 °C.
  • Examples 6 and 8 were repeated except that 3-(2-aminoethylamino)-propyltrialkoxysilane (A-1160) was used instead of A-1100.
  • the results are shown in Table 4.
  • Table 4 Run Mixing proportion Adhesion (1) (kg/25 mm) A-1160 (%) HMDA (%) 23 °C 0 °C Example 10 100 0 1.9 0.3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Laminated Bodies (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Claims (12)

  1. Structure feuilletée comprenant
    (A) une couche comprenant une résine de polyester,
    (B) une couche adhésive résultant du durcissement d'une composition qui est dépourvue de résine époxy et qui comprend (i) un composé de type organo-silicone contenant un groupement amine, représenté par la formule générale suivante (I)
    Figure imgb0005
     dans laquelle R¹ représente un groupe organique ayant un groupement amine primaire à une extrémité et un groupement hydrocarboné ; R² représente un groupement alkyle ayant de 1 à 6 atomes de carbone ou un groupement phényle ; R³ représente un groupement alkyle ayant de 1 à 6 atomes de carbone, un groupement alcoxyalkyle ayant de 1 à 6 atomes de carbone, ou un groupement acétyle ; m vaut 1 ou 2 ; n vaut 0 ou 1 ; ou son produit par condensation catalytique, et
    (ii) une diamine représentée par la formule générale suivante (II)



            H₂N-R-NH₂   (II)



    dans laquelle R représente une liaison directe, un groupement alkylènique ayant de 1 à 12 atomes de carbone, ou un groupement phénylène, la proportion du composé de type organosilicone de formule générale (I) étant de 10 à 100% pondéraux, par rapport au poids total de composé de type organosilicone de formule générale (I) et de diamine de formule générale (II), et
    (C) une couche comprenant du polyvinylbutyral, les couches (A), (B) et (C) étant stratifiées dans cet ordre.
  2. La structure feuilletée de la revendication 1 dans laquelle R¹ représente un groupement organique ayant un groupement amine primaire à son extrémité et un groupement hydrocarboné acyclique.
  3. La structure feuilletée de la revendication 1 dans laquelle R¹ représente un groupement alkyle qui a un groupement amine primaire à son extrémité et peut contenir un groupement fonctionnel dans sa chaîne.
  4. La structure feuilletée de la revendication 1 dans laquelle R¹ représente un groupement alkyle qui a un groupement amine primaire à son extrémité et peut contenir un groupement fonctionnel choisi entre -NH-, -S-, -CO-, -COO- et -C=C- dans sa chaîne.
  5. La structure feuilletée de la revendication 1 dans laquelle R¹ représente un groupement choisi entre -(CH₂)aNH₂, -(CH₂)bNH(CH₂)cNH₂, -(CH₂)dNHCONH₂, O(CH₂)eNH(CH₂)fNH(CH₂)gNH₂, et -(CH₂)hS(CH₂)iNH₂, avec a qui représente un entier valant de 1 à 6, et b, c, d, e, f, g et h, indépendamment les uns les autres, qui représentent un entier valant de 1 à 4.
  6. La structure feuilletée de l'une quelconque des revendications 1 à 5 dans laquelle m vaut 1 et n vaut 0.
  7. La structure feuilletée de l'une quelconque des revendications 1 à 6 dans laquelle la couche adhésive résulte du durcissement d'une composition comprenant (i) le produit de condensation hydrolytique d'un composé de type organosilicone contenant un groupement amine, représenté par la formule générale (I), la proportion du composé de type organosilicone de formule générale (I) étant comprise entre 10 et 95 % en poids par rapport au poids total de composé de type organosilicone et de diamine de formule générale (II).
  8. La structure feuilletée de la revendication 7 dans laquelle R représente un groupement alkylènique renfermant de 1 à 6 atomes de carbone.
  9. La structure feuilletée de la revendication 7 dans laquelle le composé de type organosilicone contenant un groupement amine, de formule générale (I) est l'un des suivants : 3-aminopropyltrialcoxysilane, 3-(2-aminoéthylamino)-propyltrialcoxysilane, 2-[(2-aminoéthyl)-thioéthyl]trialcoxysilane, 3-[2-(2-aminoéthylamino)-éthylamino]-propyltrialcoxysilane ou N-(3-trialcoxysilylpropyl)-urée.
  10. La structure feuilletée de la revendication 7 dans laquelle la couche (A) contenant une résine polyester est une pellicule étirée selon ses deux axes de téréphtalate de polyéthylène, ayant une épaisseur de 10 à 500 micromètres.
  11. La structure feuilletée de la revendication 7 dans laquelle la couche (C) contenant la résine de polyvinylbutyral est une feuille de polyvinylbutyral ayant une épaisseur de 300 à 1500 micromètres.
  12. La structure feuilletée de la revendication 7 qui comprend en plus au moins une feuille de verre stratifiée sur la surface externe de la couche (C) comprenant la résine de polyvinylbutyral qui est opposée à la couche (B).
EP88120354A 1987-12-11 1988-12-06 Structure laminée Expired - Lifetime EP0319911B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP31362687 1987-12-11
JP313626/87 1987-12-11

Publications (3)

Publication Number Publication Date
EP0319911A2 EP0319911A2 (fr) 1989-06-14
EP0319911A3 EP0319911A3 (en) 1990-09-12
EP0319911B1 true EP0319911B1 (fr) 1994-04-06

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EP88120354A Expired - Lifetime EP0319911B1 (fr) 1987-12-11 1988-12-06 Structure laminée

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US (1) US4925737A (fr)
EP (1) EP0319911B1 (fr)
DE (1) DE3888940D1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7238401B1 (en) * 2000-06-09 2007-07-03 3M Innovative Properties Company Glazing element and laminate for use in the same
JP4326679B2 (ja) * 2000-07-19 2009-09-09 リンテック株式会社 ハードコートフィルム
KR20040030118A (ko) * 2001-08-17 2004-04-08 쓰리엠 이노베이티브 프로퍼티즈 컴파니 광택 프리라미네이트, 광택 라미네이트 및 이의 제조방법
US7265176B2 (en) * 2005-01-31 2007-09-04 E. I. Du Pont De Nemours And Company Composition comprising nanoparticle TiO2 and ethylene copolymer
US20080128018A1 (en) * 2006-12-04 2008-06-05 Richard Allen Hayes Solar cells which include the use of certain poly(vinyl butyral)/film bilayer encapsulant layers with a low blocking tendency and a simplified process to produce thereof
US20090155576A1 (en) * 2007-12-18 2009-06-18 E. I. Du Pont De Nemours And Company Glass-less glazing laminates
US8080311B2 (en) * 2008-11-05 2011-12-20 E. I. Du Pont De Nemours And Company Safety glazings with improved weatherability
CN103182812A (zh) * 2011-12-30 2013-07-03 深圳富泰宏精密工业有限公司 塑料复合体及其制造方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA988965A (en) * 1972-08-28 1976-05-11 Paul T. Mattimoe Automotive glazing structure
CA1024293A (fr) * 1972-08-28 1978-01-10 E.I. Du Pont De Nemours And Company Film polymerique, structures laminees a film polymerique et articles fabriques a partir de ces structures
ZA764846B (en) * 1975-08-29 1977-04-27 Libbey Owens Ford Co Automotive glazing structure and method of producing same
US4242403A (en) * 1976-08-02 1980-12-30 Libbey-Owens-Ford Company Automotive glazing units and method of producing the same
US4469743A (en) * 1983-03-14 1984-09-04 E. I. Du Pont De Nemours And Company Polyvinyl butyral laminates

Also Published As

Publication number Publication date
US4925737A (en) 1990-05-15
EP0319911A2 (fr) 1989-06-14
EP0319911A3 (en) 1990-09-12
DE3888940D1 (de) 1994-05-11

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